Artículos de revistas
Trypanocidal Activity Of 5,6-dihydropyran-2-ones Against free Trypomastigotes Forms Of trypanosoma cruzi
Registro en:
European Journal Of Medicinal Chemistry. , v. 41, n. 10, p. 1210 - 1213, 2006.
2235234
10.1016/j.ejmech.2006.05.010
2-s2.0-33749643183
Autor
de Fatima A.
Marquissolo C.
de Albuquerque S.
Carraro-Abrahao A.A.
Pilli R.A.
Institución
Resumen
Sixteen 5,6-dihydro-2H-pyran-2-ones were evaluated in in vitro assay against trypomastigotes forms of Trypanosoma cruzi, the causative agent of Chagas' disease. A structure-activity relationship study (SAR) allowed us to establish the relevant structural features for the trypanocidal activity of goniothalamin analogues against T. cruzi. In fact, non-natural form of goniothalamin (ent-1) was threefold more potent than the natural one (1). In addition, we have identified analogues 9 and 10 (both displaying S configuration) as the highest potent compounds against T. cruzi with IC50 = 0.12 and 0.09 mM (IC50 value for crystal violet was 0.08 mM) whereas significantly lower toxicities were observed when these compounds were evaluated under LLC-MK2 lineage cells (1.38 and 4.89 mM, respectively). In addition, epoxides derivatives 12 and ent-12 were shown to be more potent than the corresponding stereoisomers 2 and ent-2 and non-natural argentilactone (ent-3, IC50 = 0.47 mM) was twofold more potent than natural argentilactone (3, IC50 = 0.94 mM). © 2006 Elsevier Masson SAS. All rights reserved. 41 10 1210 1213 Hoare, C.A., Wallace, F.G., (1996) Nature, 244, pp. 69-70 Andrade, Z.A., (1999) Mem. Inst. Oswaldo Cruz, 94, pp. 71-80 Krauth-Siegel, R.L., Bauer, H., Schirmer, R.H., (2005) Angew. Chem. Int. Ed. Engl., 44, pp. 690-715 Canesin, M.F., Barreto, A.C.P., (1997) Rev. Soc. Card. Est, São Paulo, 7, pp. 233-239 Coura, J.R., Castro, S.L., (2002) Mem. Inst. Oswaldo Cruz, 97, pp. 3-24 Cerecetto, H., Maio, R.D., Gonzales, M., Risso, M., Sagrera, G., Seoane, G., Denicola, A., Basombrio, M.A., (2000) Eur. J. Med. Chem., 35, pp. 343-350 Aguirrea, G., Boiania, L., Cerecetto, H., Fernándeza, M., Gonzáleza, M., Denicolab, A., Oteroc, L., Faundez, M., (2004) Bioorg. Med. Chem., 12, pp. 4885-4893 Aguirrea, G., Cabreraa, E., Cerecetto, H., Maioa, R.D., Gonzáleza, M., Seoanea, G., Duffautb, A., Martínez-Merino, V., (2004) Eur. J. Med. Chem., 39, pp. 421-431 Molfetta, F.A., Bruni, A.T., Honorio, K.M., da Silva, A.B.F., (2004) Eur. J. Med. Chem., 40, pp. 329-338 Keiser, J., Stich, A., Burri, C., (2001) Trends Parasitol., 17, pp. 42-49 Lee, K.-H., (2004) J. Nat. Prod., 67, pp. 273-283 Butler, M.S., (2004) J. Nat. Prod., 67, pp. 2141-2153 Clardy, J., Walsh, C., (2004) Nature, 432, pp. 829-837 Blázquez, M.A., Bermejo, A., Zafra-Polo, M.C., Cortes, D., (1999) Phytochem. Anal., 10, pp. 161-170 Meenakshii, N., Lee, A., Azimahtol, H.L.P., Hasidah, S., (2000) Malays, Appl. Biol., 29, pp. 121-126 de Fátima, A., Kohn, L.K., de Carvalho, J.E., Pilli, R.A., (2006) Bioorg. Med. Chem., 14, pp. 622-631 Mosaddik, M.A., Hauqe, M.E., (2003) Phytotherapy Res., 17, pp. 1155-1157 Kabir, K.E., Khan, A.R., Mosaddik, M.A., (2003) Appl. Ent., 127, pp. 112-115 Mosaddik, M.A., Hauqe, M.E., Rashid, M.A., (2000) Biochem. Systemat. Ecol., 28, pp. 1039-1040 Sam, T.W., Sew-Yeu, C., Matsjeh, S., Gan, E.K., Razak, D., Mohamed, A.L., (1987) Tetrahedron Lett., 28, pp. 2541-2544 Lan, Y.H., Chang, F.R., Yu, J.H., Yang, Y.L., Chang, Y.L., Lee, S.J., Wu, Y.C., (2003) J. Nat. Prod., 66, pp. 487-490 Goh, S.H., Ee, G.C.L., Chuah, C.H., Wei, C., Mak, T.C.W., (1995) Aust. J. Chem., 48, pp. 199-205 Priestap, H.A., Bonafede, J.D., Ruveda, E.A., (1977) Phytochemistry, 16, pp. 1579-1582 Matsuda, M., Endo, Y., Fushiya, S., Endo, T., Nozoe, S., (1994) Heterocycles, 38, pp. 1229-1232 Waechter, A.I., Ferreira, M.E., Fournet, A., Arias, A.R., Nakayama, H., Torres, S., Hocquemiller, R., Cave, A., (1997) Planta Med., 63, pp. 433-435 Carmona, D., Sáez, J., Granados, H., Pérez, E., Blair, S., Angulo, A., Figadere, B., (2003) Nat. Prod. Res., 17, pp. 275-280 de Fátima, A., Pilli, R.A., (2003) Arkivoc, 10, pp. 118-126 de Fátima, A., Pilli, R.A., (2003) Tetrahedron Lett., 44, pp. 8721-8724 de Fátima, A., Kohn, L.K., Antonio, M.A., de Carvalho, J.E., Pilli, R.A., (2004) Bioorg. Med. Chem., 12, pp. 5437-5442 de Fátima, A., Kohn, L.K., Antonio, M.A., de Carvalho, J.E., Pilli, R.A., (2005) Bioorg. Med. Chem., 13, pp. 2927-2933 Neto, A.G., da Silva Filho, A.A., Costa, J.M.L.C., Vinholis, A.H.C., Souza, G.H.B., Cunha, W.R., Silva, M.L.A.E., Bastos, J.K., (2004) Phytomed., 11, pp. 622-665 Ambrozin, A.R.P., Mafezoli, J., Vieira, P.C., Fernandes, J.B., da Silva, M.F.G.F., Ellena, J.A., Albuquerque, S., (2005) J. Braz. Chem. Soc., 16, pp. 434-439 de Souza, V.A., da Silva, R., Pereira, A.C., Royo, V.A., Saraiva, J., Montanheiro, M., de Souza, G.H.B., Silva, M.L.A., (2005) Bioorg. Med. Chem. Lett., 15, pp. 303-307 Mosmann, T., (1983) J. Immunol. Methods, 65, pp. 55-63